t-Butyl bromide → Ethyl 2-(tert-butoxy)-2-(2-phenyl-1-benzothiophen-3-yl)acetate

HRID 590959Notes

Reaction equation

HRID 590959 reaction equation
[OH:1][CH:2]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:23](Br)([CH3:26])([CH3:25])[CH3:24]>C1CCCCC1.[Ag-]=O>[C:23]([O:1][CH:2]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 10485t-Butyl bromideHCID 70813709Ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate

Product 1

HCID 70813740Ethyl 2-(tert-butoxy)-2-(2-phenyl-1-benzothiophen-3-yl)acetateYield 13.3%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 8078CyclohexaneSolvent

Procedure

A mixture of ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate (2c) (190 mg, 0.6 mmol), silver (I) oxide (417 mg, 1.8 mmol) and tertbutylbromide (360 μL, 3.2 mmol) in cyclohexane (5 mL) was vigorously stirred for 2 hours. The reaction mixture was then filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired ether oxide (2d) as a white solid (30 mg, 0.08 mmol, 13%).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-0cf6773b6f454af7bc07e8bcf90b7279
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

Loading…